HCID 23365872, compound → HCID 178497910, compound

HRID 1756409Notes

Reaction equation

HRID 1756409 reaction equation
C([O:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([NH:18][C:19](=[O:26])[CH2:20][CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:15][CH:16]=2)[N:11]([CH2:27][C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][C:29]=2[O:38][CH3:39])[N:10]=1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[CH:21]1([CH2:20][C:19]([NH:18][C:14]2[CH:13]=[C:12]3[C:17]([C:9]([OH:8])=[N:10][N:11]3[CH2:27][C:28]3[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][C:29]=3[O:38][CH3:39])=[CH:16][CH:15]=2)=[O:26])[CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

4

Reactant 1

HCID 23365872HCID 23365872, compound

Product 1

HCID 178497910HCID 178497910, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 4-[3-benzyloxy-6-(2-cyclopentylacetamido)indazol-1-ylmethyl]-3-methoxybenzoate (BB) (5.0 g.), and palladium-on-carbon (5% w/w, 1.25 g.), in ethyl acetate (190 ml.), was hydrogenated at 1.1 bar for 7.5 hours. The catalyst was removed by filtration through diatomaceous earth, washing the filter cake with ethanol, the filtrate partially evaporated, and the residue allowed to crystallize to give the title compound (2.56 g., 62%), as a solid, m.p. 242°-245° C.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. washwashing the filter cake with ethanol
  3. customthe filtrate partially evaporated
  4. customto crystallize

Sources & evidence

ORD record
ord-bbab5f2f2f16444c9d55c7bd639c10ff
Source dataset
uspto-grants-1995_08
Patent number
US05440035

Reaction notes

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